2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67126222, compound

HRID 514055Notes

Reaction equation

HRID 514055 reaction equation
[Br:1][C:2]1[CH:3]([CH3:21])[CH2:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[CH:9][CH:8]=[C:7]([O:19][CH3:20])[CH:6]=2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:21])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:19][CH3:20])[CH:6]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67126221HCID 67126221, compound

Product 1

HCID 67126222HCID 67126222, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-bromo-4-(4-chlorophenyl)-7-methoxy-2-methyl-1,2-dihydronaphthalene (5.5 g, 15.1 mmol) in toluene (100 mL) was vacuum flushed with Ar. DDQ (5.2 g, 22.7 mmol) was added and the mixture heated to reflux for 1.5 h. The heterogeneous red-brown mixture was cooled to room temperature and the toluene removed in vacuo. The resulting residue was taken up in DCM (300 mL) and filtered to remove precipitated DDHQ. The resulting mother liquor was absorbed on silica gel and purified by Yamazen column chromatography (15% DCM/Hex) to afford 5.21 g (95%) of the title compound as an amorphous yellow solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.66 (s, 1H); 7.49 (br d, J=2 Hz, 2H); 7.24-7.18 (m, 3H); 7.07 (d, J=2 Hz, 1H); 6.97 (dd, J=9.2, 2 Hz, 1H); 3.91 (s, 3H); 2.60 (s, 3H).

Workup

  1. customflushed with Ar
  2. temperaturethe mixture heated
  3. temperatureto reflux for 1.5 h
  4. customthe toluene removed in vacuo
  5. filtrationfiltered
  6. customto remove
  7. customprecipitated DDHQ
  8. customThe resulting mother liquor was absorbed on silica gel
  9. custompurified by Yamazen column chromatography (15% DCM/Hex)

Sources & evidence

ORD record
ord-4000ded6231b4454abe0845866e9424d
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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